Dichloromethane → HCID 178482257, compound

HRID 1189672Notes

Reaction equation

HRID 1189672 reaction equation
[F:1][C:2]([F:30])([F:29])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:28])[C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:27])[CH2:23][C:24]([NH2:26])=O)[CH2:5][CH2:4]1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.C(Cl)Cl.C1COCC1>C([O-])(O)=O.[Na+]>[F:1][C:2]([F:29])([F:30])[C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:28])[C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[C:14]([NH:20][CH3:21])=[CH:13][C:12]=2[N:22]([CH3:27])[CH2:23][C:24]#[N:26])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 178482258HCID 178482258, compound

Product 1

HCID 178482257HCID 178482257, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of N-(trans-4-trifluoromethyl-cyclohexyl)-2-[N-methyl-N-aminocarbonylmethyl-amino]-4-methylamino-5-nitro-benzoic acid amide (compound IIIa, 45 mg, 0.104 mmol), Burgess reagent (27 mg, 0.11 mmol, +20 mg after 0.5 h, +15 mg after 2.5 h, +20 mg after 16 h), DCM (2 mL) and THF (2 mL) is stirred for 2.5 h at rt, then for 13.5 h at 40° C. and then for 2 h at reflux. The mixture is diluted with sat aq NaHCO3, extracted with EtOAc and the combined organic phases are dried with Na2SO4, filtered and concentrated and directly used in the next step. Yield: 80 mg. HPLC Rt=1.36 min (method A). MS m/z: 414 [M+H]+.

Workup

  1. waitfor 13.5 h at 40° C.
  2. temperaturefor 2 h at reflux
  3. extractionextracted with EtOAc
  4. dry with materialthe combined organic phases are dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a8762f9aa2fc4f048fdc6c1917a8854a
Source dataset
uspto-grants-2014_03
Patent number
US08674113B2

Reaction notes

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